1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3,5-Dimethyl-isoxazole-4-carboxylic acid [4-chloro-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amide

HRID 1774859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1774859
Cl.[NH2:2][CH2:3][C:4]1[C:5]([Cl:22])=[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)[CH:7]=[N:8][CH:9]=1.CCN=C=NCCCN(C)C.OC1C2N=NNC=2C=CC=1.CCN(C(C)C)C(C)C.[CH3:53][C:54]1[C:58]([C:59](O)=[O:60])=[C:57]([CH3:62])[O:56][N:55]=1.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:22][C:5]1[C:6]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH3:20])[C:15](=[O:21])[CH2:14][CH2:13]3)=[CH:7][N:8]=[CH:9][C:4]=1[CH2:3][NH:2][C:59]([C:58]1[C:54]([CH3:53])=[N:55][O:56][C:57]=1[CH3:62])=[O:60]

Komponenten

9

Edukt 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 756363,5-Dimethylisoxazole-4-carboxylic acidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 866792006-(5-Aminomethyl-4-chloro-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochlorideHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 866792023,5-Dimethyl-isoxazole-4-carboxylic acid [4-chloro-5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-ylmethyl]-amideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 6-(5-aminomethyl-4-chloro-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride (example 218, 0.05 g, 0.148 mmol) in dry DMF (1 mL) were added EDCI (0.034 g, 0.077 mmol), hydroxybenzotriazole (0.017 g, 0.077 mmol), Hünig's base (0.057 g, 0.443 mmol) and 3,5-dimethyl-isoxazole-4-carboxylic acid (0.021 g, 0.148 mmol) and the resulting solution was stirred at room temperature for 2 h. The reaction mixture was diluted with EtOAc, poured into sat. NaHCO3 solution (10 mL) and extracted with EtOAc (2×20 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.03 g, 48%) as a colorless solid. MS: 425.4 (M+H+).

Aufarbeitung

  1. extractionextracted with EtOAc (2×20 mL)
  2. dry with materialCombined organics were dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by silica gel flash chromatography
  6. washeluting with a 0 to 5% MeOH-DCM gradient

Quellen und Nachweise

ORD-Eintrag
ord-14236c5db8b24e8283b2ac4e2a664f9f
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260408B2

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